diff --git a/osu.Game.Rulesets.Osu/Objects/Drawables/Connections/FollowPoint.cs b/osu.Game.Rulesets.Osu/Objects/Drawables/Connections/FollowPoint.cs
index aacf3ee08d..a2a23e9ff7 100644
--- a/osu.Game.Rulesets.Osu/Objects/Drawables/Connections/FollowPoint.cs
+++ b/osu.Game.Rulesets.Osu/Objects/Drawables/Connections/FollowPoint.cs
@@ -41,7 +41,7 @@ namespace osu.Game.Rulesets.Osu.Objects.Drawables.Connections
                     Anchor = Anchor.Centre,
                     Alpha = 0.5f,
                 }
-            }, restrictSize: false);
+            }, confineMode: ConfineMode.NoScaling);
         }
     }
 }
diff --git a/osu.Game.Rulesets.Osu/Objects/Drawables/DrawableRepeatPoint.cs b/osu.Game.Rulesets.Osu/Objects/Drawables/DrawableRepeatPoint.cs
index cce6dfe106..cf6f05a604 100644
--- a/osu.Game.Rulesets.Osu/Objects/Drawables/DrawableRepeatPoint.cs
+++ b/osu.Game.Rulesets.Osu/Objects/Drawables/DrawableRepeatPoint.cs
@@ -37,7 +37,7 @@ namespace osu.Game.Rulesets.Osu.Objects.Drawables
                 {
                     RelativeSizeAxes = Axes.Both,
                     Icon = FontAwesome.Solid.ChevronRight
-                }, restrictSize: false)
+                })
             };
         }
 
diff --git a/osu.Game.Rulesets.Osu/Objects/Drawables/DrawableSliderTick.cs b/osu.Game.Rulesets.Osu/Objects/Drawables/DrawableSliderTick.cs
index 72b648bfd0..01ef1eb3e0 100644
--- a/osu.Game.Rulesets.Osu/Objects/Drawables/DrawableSliderTick.cs
+++ b/osu.Game.Rulesets.Osu/Objects/Drawables/DrawableSliderTick.cs
@@ -23,7 +23,7 @@ namespace osu.Game.Rulesets.Osu.Objects.Drawables
         public DrawableSliderTick(SliderTick sliderTick)
             : base(sliderTick)
         {
-            Size = new Vector2(16) * sliderTick.Scale;
+            Size = new Vector2(16 * sliderTick.Scale);
             Origin = Anchor.Centre;
 
             InternalChildren = new Drawable[]
@@ -44,7 +44,7 @@ namespace osu.Game.Rulesets.Osu.Objects.Drawables
                         Colour = AccentColour,
                         Alpha = 0.3f,
                     }
-                }, restrictSize: false)
+                })
             };
         }
 
diff --git a/osu.Game.Rulesets.Osu/Objects/Drawables/Pieces/NumberPiece.cs b/osu.Game.Rulesets.Osu/Objects/Drawables/Pieces/NumberPiece.cs
index 84034d3ee9..e8dc63abca 100644
--- a/osu.Game.Rulesets.Osu/Objects/Drawables/Pieces/NumberPiece.cs
+++ b/osu.Game.Rulesets.Osu/Objects/Drawables/Pieces/NumberPiece.cs
@@ -46,7 +46,7 @@ namespace osu.Game.Rulesets.Osu.Objects.Drawables.Pieces
                 {
                     Font = OsuFont.Numeric.With(size: 40),
                     UseFullGlyphHeight = false,
-                }, restrictSize: false)
+                }, confineMode: ConfineMode.NoScaling)
                 {
                     Text = @"1"
                 }
diff --git a/osu.Game.Rulesets.Osu/UI/Cursor/OsuCursor.cs b/osu.Game.Rulesets.Osu/UI/Cursor/OsuCursor.cs
index 27546fa424..b3492a2b31 100644
--- a/osu.Game.Rulesets.Osu/UI/Cursor/OsuCursor.cs
+++ b/osu.Game.Rulesets.Osu/UI/Cursor/OsuCursor.cs
@@ -101,7 +101,7 @@ namespace osu.Game.Rulesets.Osu.UI.Cursor
                             },
                         },
                     }
-                }, restrictSize: false)
+                })
                 {
                     Origin = Anchor.Centre,
                     Anchor = Anchor.Centre,
diff --git a/osu.Game.Tests/Visual/Gameplay/TestSceneSkinReloadable.cs b/osu.Game.Tests/Visual/Gameplay/TestSceneSkinReloadable.cs
index c7a0df6e9f..af03ddc65c 100644
--- a/osu.Game.Tests/Visual/Gameplay/TestSceneSkinReloadable.cs
+++ b/osu.Game.Tests/Visual/Gameplay/TestSceneSkinReloadable.cs
@@ -92,8 +92,8 @@ namespace osu.Game.Tests.Visual.Gameplay
             public new Drawable Drawable => base.Drawable;
             public int SkinChangedCount { get; private set; }
 
-            public SkinConsumer(string name, Func<string, Drawable> defaultImplementation, Func<ISkinSource, bool> allowFallback = null, bool restrictSize = true)
-                : base(name, defaultImplementation, allowFallback, restrictSize)
+            public SkinConsumer(string name, Func<string, Drawable> defaultImplementation, Func<ISkinSource, bool> allowFallback = null)
+                : base(name, defaultImplementation, allowFallback)
             {
             }
 
diff --git a/osu.Game/Rulesets/Judgements/DrawableJudgement.cs b/osu.Game/Rulesets/Judgements/DrawableJudgement.cs
index 2150726a42..61c2644c6f 100644
--- a/osu.Game/Rulesets/Judgements/DrawableJudgement.cs
+++ b/osu.Game/Rulesets/Judgements/DrawableJudgement.cs
@@ -67,7 +67,7 @@ namespace osu.Game.Rulesets.Judgements
                     Font = OsuFont.Numeric.With(size: 12),
                     Colour = judgementColour(Result.Type),
                     Scale = new Vector2(0.85f, 1),
-                }, restrictSize: false)
+                })
             };
         }
 
diff --git a/osu.Game/Skinning/SkinnableDrawable.cs b/osu.Game/Skinning/SkinnableDrawable.cs
index 995cb15136..a30bdbd2dc 100644
--- a/osu.Game/Skinning/SkinnableDrawable.cs
+++ b/osu.Game/Skinning/SkinnableDrawable.cs
@@ -9,8 +9,8 @@ namespace osu.Game.Skinning
 {
     public class SkinnableDrawable : SkinnableDrawable<Drawable>
     {
-        public SkinnableDrawable(string name, Func<string, Drawable> defaultImplementation, Func<ISkinSource, bool> allowFallback = null, bool restrictSize = true)
-            : base(name, defaultImplementation, allowFallback, restrictSize)
+        public SkinnableDrawable(string name, Func<string, Drawable> defaultImplementation, Func<ISkinSource, bool> allowFallback = null, ConfineMode confineMode = ConfineMode.ScaleDownToFit)
+            : base(name, defaultImplementation, allowFallback, confineMode)
         {
         }
     }
@@ -29,7 +29,7 @@ namespace osu.Game.Skinning
 
         private readonly string componentName;
 
-        private readonly bool restrictSize;
+        private readonly ConfineMode confineMode;
 
         /// <summary>
         /// Create a new skinnable drawable.
@@ -37,18 +37,18 @@ namespace osu.Game.Skinning
         /// <param name="name">The namespace-complete resource name for this skinnable element.</param>
         /// <param name="defaultImplementation">A function to create the default skin implementation of this element.</param>
         /// <param name="allowFallback">A conditional to decide whether to allow fallback to the default implementation if a skinned element is not present.</param>
-        /// <param name="restrictSize">Whether a user-skin drawable should be limited to the size of our parent.</param>
-        public SkinnableDrawable(string name, Func<string, T> defaultImplementation, Func<ISkinSource, bool> allowFallback = null, bool restrictSize = true)
-            : this(name, allowFallback, restrictSize)
+        /// <param name="confineMode">How (if at all) the <see cref="Drawable"/> should be resize to fit within our own bounds.</param>
+        public SkinnableDrawable(string name, Func<string, T> defaultImplementation, Func<ISkinSource, bool> allowFallback = null, ConfineMode confineMode = ConfineMode.ScaleDownToFit)
+            : this(name, allowFallback, confineMode)
         {
             createDefault = defaultImplementation;
         }
 
-        protected SkinnableDrawable(string name, Func<ISkinSource, bool> allowFallback = null, bool restrictSize = true)
+        protected SkinnableDrawable(string name, Func<ISkinSource, bool> allowFallback = null, ConfineMode confineMode = ConfineMode.ScaleDownToFit)
             : base(allowFallback)
         {
             componentName = name;
-            this.restrictSize = restrictSize;
+            this.confineMode = confineMode;
 
             RelativeSizeAxes = Axes.Both;
         }
@@ -58,7 +58,7 @@ namespace osu.Game.Skinning
         protected virtual T CreateDefault(string name) => createDefault(name);
 
         /// <summary>
-        /// Whether to apply size restrictions (specified via <see cref="restrictSize"/>) to the default implementation.
+        /// Whether to apply size restrictions (specified via <see cref="confineMode"/>) to the default implementation.
         /// </summary>
         protected virtual bool ApplySizeRestrictionsToDefault => false;
 
@@ -76,12 +76,18 @@ namespace osu.Game.Skinning
 
             if (Drawable != null)
             {
-                if (restrictSize && (!isDefault || ApplySizeRestrictionsToDefault))
+                if (confineMode != ConfineMode.NoScaling && (!isDefault || ApplySizeRestrictionsToDefault))
                 {
-                    Drawable.RelativeSizeAxes = Axes.Both;
-                    Drawable.Size = Vector2.One;
-                    Drawable.Scale = Vector2.One;
-                    Drawable.FillMode = FillMode.Fit;
+                    bool applyScaling = confineMode == ConfineMode.ScaleToFit ||
+                                        (confineMode == ConfineMode.ScaleDownToFit && (Drawable.DrawSize.X > DrawSize.X || Drawable.DrawSize.Y > DrawSize.Y));
+
+                    if (applyScaling)
+                    {
+                        Drawable.RelativeSizeAxes = Axes.Both;
+                        Drawable.Size = Vector2.One;
+                        Drawable.Scale = Vector2.One;
+                        Drawable.FillMode = FillMode.Fit;
+                    }
                 }
 
                 Drawable.Origin = Anchor.Centre;
@@ -93,4 +99,14 @@ namespace osu.Game.Skinning
                 ClearInternal();
         }
     }
+
+    public enum ConfineMode
+    {
+        /// <summary>
+        /// Don't apply any scaling. This allows the user element to be of any size, exceeding specified bounds.
+        /// </summary>
+        NoScaling,
+        ScaleDownToFit,
+        ScaleToFit,
+    }
 }
diff --git a/osu.Game/Skinning/SkinnableSprite.cs b/osu.Game/Skinning/SkinnableSprite.cs
index ceb1ed0f70..1716ec71de 100644
--- a/osu.Game/Skinning/SkinnableSprite.cs
+++ b/osu.Game/Skinning/SkinnableSprite.cs
@@ -18,8 +18,8 @@ namespace osu.Game.Skinning
         [Resolved]
         private TextureStore textures { get; set; }
 
-        public SkinnableSprite(string name, Func<ISkinSource, bool> allowFallback = null, bool restrictSize = true)
-            : base(name, allowFallback, restrictSize)
+        public SkinnableSprite(string name, Func<ISkinSource, bool> allowFallback = null, ConfineMode confineMode = ConfineMode.ScaleDownToFit)
+            : base(name, allowFallback, confineMode)
         {
         }
 
diff --git a/osu.Game/Skinning/SkinnableSpriteText.cs b/osu.Game/Skinning/SkinnableSpriteText.cs
index 36e646d743..d12a6f74f7 100644
--- a/osu.Game/Skinning/SkinnableSpriteText.cs
+++ b/osu.Game/Skinning/SkinnableSpriteText.cs
@@ -8,8 +8,8 @@ namespace osu.Game.Skinning
 {
     public class SkinnableSpriteText : SkinnableDrawable<SpriteText>, IHasText
     {
-        public SkinnableSpriteText(string name, Func<string, SpriteText> defaultImplementation, Func<ISkinSource, bool> allowFallback = null, bool restrictSize = true)
-            : base(name, defaultImplementation, allowFallback, restrictSize)
+        public SkinnableSpriteText(string name, Func<string, SpriteText> defaultImplementation, Func<ISkinSource, bool> allowFallback = null, ConfineMode confineMode = ConfineMode.ScaleDownToFit)
+            : base(name, defaultImplementation, allowFallback, confineMode)
         {
         }